Buchwald–Hartwig amination: 3-Bromoanisole → 1-(3-Methoxyphenyl)piperidine-4-carbonitrile
54% yield, run at 100 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 3-Bromoanisole | C₇H₇BrO | |
| Reactant | 4-Cyanopiperidine | C₆H₁₀N₂ | |
| Reagent | lithium bis(trimethylsilyl)azanide | C₆H₁₈LiNSi₂ | |
| Catalyst | 2,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo(3.3.3)undecane | C₁₈H₃₉N₄P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | 1-(3-Methoxyphenyl)piperidine-4-carbonitrile | C₁₃H₁₆N₂O | 54.48% |
Conditions
- Temperature
- 100 °C
Yield
- 54% of 1-(3-Methoxyphenyl)piperidine-4-carbonitrile.
Procedure
Copied from the source record, unedited
piperidine-4-carbonitrile (0.353 g, 3.21 mmol); 1-bromo-3-methoxybenzene (0.339 mL, 2.67 mmol) and diacetoxypalladium (0.120 g, 0.53 mmol) were thoroughly placed under an inert atmoshere. To this was added 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (0.037 g, 0.11 mmol); LITHIUM BIS(TRIMETHYLSILYL)AMIDE (6.15 mL, 6.15 mmol) and toluene (10 mL). The resultant mixture was stirred overnight at 100 °C (suspect that it did not need overnight. Equal vol of DCM was added and the reaction mixture filtered. Removal of the solvent under reduced pressure gave a dark brown gum. The crude product was purified by flash Silica chromatography {CombiFlash Companion - Presearch Ltd}, column size = 12 g , flow rate = 30 ml / min, elution gradient 0 to 30% EtOAc in isohexane over 10 m
The source
This record comes from experimental reaction archive (ord-fa6037d0d8a544539857cac2da5223a4). Open the source and check it against what is on this page.
experimental reaction archive record ord-fa6037d0d8a544539857cac2da5223a4 from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.
How to read this record
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